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I first met Elliot through his passion for jug band music and the annual Battle of the Jug Bands for which he is Master of Ceremonies. He shares a similar passion for fishing and for all things Dylan. He’s spent a lifetime doing portraits at art fairs, and brings a perspective to this kind of work from decades of first-hand experience.

EN: When did you start drawing portraits?  

Elliot Silberman: The early 70’s, while working at Bethany Children’s Home. I had my own office with a piano, and started sketching the teens mostly, as they came in and out. That’s how I started. There were no Arts and Crafts shows then. Sidewalk sales, West Duluth Days celebration, the Folk Festival was really the only one. At some point then I approached the commander of Goldfine’s by the bridge, asking her if I could set up by the cafe upstairs and do 5 minute portrait sketches on weekends. Did that all summer, later trying the Canal Park area; I was hassled a bit by local police (“Got a permit, young man?”) Grandma’s had a couple of barber chairs, and allowed me to sketch there for a spell.  

EN: What kind of setup did you have?

ES: I don’t recall having much of a display back then. Just two chairs, and a small easel with one framed sample on it. I charged $1 back then, happy to get it. Never did make more than $30 a day at Canal Park.
During raising a family, with 3 kids, I taught some adult education classes, too. Guitar picking, watercolor painting.  We had been living in a renovated, add-on cabin, with no overhead. I remember the first art show in Canal Park, I made $50 a day for two days. I said to my wife, “Honey, if I can make $300 a month, I think we can make it.” Life insurance, health insurance, car insurance, what was that? We had a garden, too, and a retired nurse down the road who we could bounce health-related questions off, explaining the symptoms from the kids being sick.    

EN: How has the art show scene changed since those early days?

ES: Now, art shows have changed el mucho.  The first 20 years were very exciting. Most are average people who wouldn’t go to galleries to view art. They loved shopping in grassy parks. I was charging $2 or $3 a sketch at that time. I never would have ventured into public sketching if I would have started charging $5 or more per sketch. That way if I screwed up, which I did, I would give it 3 shots.  If I didn’t get a sketch that had a resemblance, “See ya. No charge!” I took the hit.  
It was hard not knowing what to expect from myself. Soon every mall had two arts and crafts shows. The two biggest malls in Minneapolis-St. Paul charged $15 for a four-day show. This was very new then, and brought lots of people into the malls. I did very well. Slept on a friend’s couch. I would sketch for hours, people lined up behind me. It was great. And I was improving all the time. At this time caricaturists started showing up everywhere. It became hard to compete with them... I’m still trying to outrun them as they venture out, like I was doing. I knew two caricature artists who started training others in their trade, sending them out by fives to high school parties, which I was doing. I found what I enjoyed most is casual portraits. That is, no fake smiles, no pressure.  
About this time I got into the Minnesota Renaissance Festival as a peddler. Everything in a pack, on the hoof.  It was embarrassing to wear tights, but I survived.  November thru April, I did malls, and I did well. From Rice Lake, Wisconsin and thru the Midwest, I got spoiled.  

EN: When did things begin to change?

ES: The art show was one of the greatest ideas brought forth. It gave the average person a chance to market their work, and the average person to buy art and crafts, especially functional pottery.   
The first 20 were great; the next 20 we could see the handwriting on the wall. As with most things, they went more commercial, little by little. Too many shows too close together, all the time. Malls saw this first, it brought people into the mall, then people slowly got numb to the deal. I had very little overhead, no rent, no health coverage, no retirement, no car insurance too. That made it much easier for me to survive. Otherwise the only other way was to get a job and work your craft on the side.  

EN: You have a special approach when drawing children. Can you elaborate on that bit?

ES: Early on, when in malls, I saw many mothers ‘n babies ‘n kids there, so I made a sign, CHILDREN, MY SPECIALTY, or “All Moving Targets Welcome.” Now if I was cheap, $3. each, it was my way out if I didn’t nail the sketch, or the kid threw a fit. I just took the hit and said, “That’s all right ma’am. No charge.” Or “Two or three tries?”  It was just my time I lost. Time was on my side.    
Even with little ones, here is what I say while making eye contact, “This is going to be fun but hard. I need you to stare at me for 5 minutes.” With eye contact, I ask them, “Want to know what I know about you already? You’re listening to me. That’s great!” I’m now centering the portrait on my paper, while I’m being stared at. “Wanna know what else I know about you? You’re paying attention. That is sooo cool.  Because when your paying attention, every day, that’s how you find out about things, things you might really like to make a part of your life. When some things get your attention, that means, check it out. You can build your life around things that make your life rich. Fun. Interesting. Is that cool or what?”  
Of course I adapt to their age, but I believe in planting seeds. Parents know, that their kid won’t always listen to them like they do to me. They’re not dumb. I get each kid for 5 minutes. Might as well make use of that time, besides sketching. Plant some seeds.